3 Acetamido-2-butanone

Butane, 1,4-diiodo-, 30, 33 2-Butanone, 3-acetamido-, 33,1 n-BuTYLACETYLENE, 30, IS tert-Butyl alcohol, 30, 19, 20 32, 20 ierl-Butylbenzene, 32, 91 n-Butyl bromide, 30, 16 tert-Butyl hypochlorite, 32, 20 n-Butyl iodide, 30, 34 Butylketene dimer, 31, 71 -ter -Butylphenyl salicylate, 32, 26 Butyrchloral, 33, IS Butyric acid, a, y-dicyano-o-phenyl-, ethyl ester, 30, 80... 

Butadiene monoxide, 31, 3 Butane, 1,4-dhodo-, 30, 33 1,4-dinitro-, 34, 37 2-Butanone, 3-acetamido-, 33,1 terl-Butyl acetate, 34, 28 tt-BuTYLACETYI.ENE, 30, IS... 

This method, an adaptation of a previously described procedure,2- 8-4 has been used with a variety of amino acids and anhydrides to give the following products 1-phenyl-1-propionamidO-2-butanone (75%) 6 acetamidoacetylacetone (60%) 6 N-methyl-acetamidoacetone 6 l-phenyl-2-acetamido-3-butanone (79%) 7 l-phenyl-2-propionamido-3-pentanone (41%) 7 l-phenyl-2-butyr-amido-3-hexanone (27%) 7 a-benzamidopropiophenone (42%) 7 a-benzamido-/3-phenylpropiophenone (44%) 7 1 -phenyl-1 -aceta-midoacetone (72-90%) 8-91-phenyl-1-benzamidoacetone (65%) 8 l-phenyl-2-benzamido-3-butanone (78%) 8 3-benzamido-2-buta-none (65-88%) 8 and 3-acetamido-5-methyl-2-hexanone (73%).10... 

A mixture of 156.6 g. (159 ml., 1.98 moles) of pyridine (Note 1), 239.9 g. (224 ml., 2.35 moles) of acetic anhydride (Note 2), and 35.1 g. (0.394 mole) of vacuum-dried alanine (Notes 3 and 4) is heated with stirring (Note 5) on the steam bath for 6 hours after solution is complete (Note 6). The excess pyridine and acetic anhydride, and the acetic acid, are removed at reduced pressure. The residue is distilled through a 15-cm. column, packed with glass helices, to give 41.5-47.5 g. of crude product, boiling at 110-125°/3 mm. Refractionation gives 41-45 g. (81-88%) of 3-acetamido-2-butanone b.p. 102-106°/2 mm. 1.4558-1.4561 (Note 7). 

Fry und Rapaport (S6) erhielten mit Alanin-[l-14C] bzw. Phenyl-alanin-f 1-14C] und inaktivem Essigsaureanhydrid. ein radioaktives Kohlendioxyd, das dieselbe molare Aktivitat wie die Aminosaure hatte. Das 1 -Phenyl-2-acetamino-butanon bzw. das 3-Acetamido-butanon-2 waren nichtradioaktiv. Dadurch wird der erste Mechanismus ausge-schlossen. 

This preparation is based on the procedure used to synthesize 3-acetamido-2-butanone. Aminoacetone hydrochloride has been... 

C-Acylation. A general reaction discovered by Dakin and West is illustrated by the reaetion of alanine with acetic anhydride and pyridine to afford 2-acetamido-2-butanone and carbon dioxide. The mixture is stirred on the steam bath until... 

Me glycoside, N,2,4,6-tetra-Ac Methyl 3-acetamido-2,4,6-tri-0-acetyl-3-deoxy-fi-D-allopyranoside C15H23NO9 361.348 Cryst. (butanone). Mp 179°. [a]o -41.2 (c, 2 in CHCI3). 

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